N-substituted fatty acid amide lubricants

ABSTRACT

This invention relates to N-acylmorpholines and N-mono and N,Ndisubstituted fatty acid amides and to similar derivatives of epithioamides which are useful as base and extreme pressure lubricants and additives.

United States Patent Magne et al.

1*Mar. 25, 1975 N-SUBSTITUTED FATTY ACID AMIDE LUBRICANTS Inventors: Frank C. Magne; Robert R. Mod;

Gene Sumrell, all of New Orleans, La.

The United States of America as represented by the Secretary of Agriculture, Washington, DC.

Assignee:

Notice: The portion of the term of this patent subsequent to July 17, 1990, has been disclaimed.

Filed: Feb. 21, 1973 Appl. No: 334,318

Related U.S. Application Data Continuation-in-part of Ser. No. 176,734, Aug. 31, 1971, Pat. No. 3,746,644.

U.S. Cl 252/475, 252/484; 252/486 Int. Cl C10m l/38 Field of Search 252/482, 48.4, 48.6

Primary Examiner-Patrick P. Garvin Assistant ExaminerAndrew H. Metz Attorney, Agent, or Firm-M. Howard Silverstein; Max D. Hensley {57] ABSTRACT This invention relates to N-acylmorpholines and N- mono and N,N-disubstituted fatty acid' amides and to similar derivatives of epithioamides which are useful base and extreme pressure lubricants and additives.

41 Claims, N0 Drawings N-SUBSTITUTED FATTY ACID AMIDE LUBRICANTS A non-exclusive, irrevocable, royalty-free license in the invention herein described, throughout the world for all purposes of the United States Government, with the power to grant sublicenses for such purposes, is hereby granted to the Government of the United States of America.

This application is a continuation-in-part of Ser. No. 176,734 filed Aug. 31, 1971, said 176,734 now US. Pat. No. 3,746,644

This invention relates to certain compounds which are N-fatty acyl derivatives of primary and secondary amine and N-substituted acyl derivatives of primary and secondary amines which have exhibited utility as base lubricants, extreme pressure lubricants or lube additives. More particularly, this invention relates to N- and NN-disubstituted long chain allphatic amides the acyl component of which is a normal, branched, or substituted alkenoic or alkanoic acyl group containing from 16 to 22 carbon atoms the amide nitrogen of which may be derived from an alkyl amine, dialkyl amine, alkyl-alkoxyalkylamine, dialkoxyalkylamine or nitrogen heteroalicyclic. Typical amines are butylamines, dibutylamines, N-methyl-alkoxyethyl amine, diethoxyethyl amine, and morpholine. The acyl substituent referred to may be divalent sulfur or pentavalent phosphorous.

We have discovered that many of the simple N-alkyl and N,N-dialkyl or N-alkyl-N-alkoxyalkyl amides of the C to C alkeneoic or alkanoic fatty acids are good base lubricants. We have further discovered that the introduction of divalent sulfur into the fatty acid moiety imparts excellent extreme pressure lubricant characteristics to such compounds. We have also found this to be true for glycerides and simple esters even when the divalent sulfur substituent group is in the alkyl moiety. ln particular we have found the epithio group to be most effective. We have also observed that the introduction ofboth hydroxy and alkyl phosphato groupings alpha to each other also imparts extreme pressure lubricant characteristics to the compound.

1n addition it was noted that the above hydroxyphosphato compound and its mercapto analog N- [9( 10 )-mercapto-(9) lO-dibutylphosphato]stearamide were effective antiwear compounds and additives.

Included among the specific compounds operable as base lubricants are N-methyl-N-butyloleamide, N-ethoxyethoxyethoxy propyloleamide, N- ethoxyethoxy propyloleamide, N-

methoxyisopropyloleamide, N-methoxyethyloleamide. Compounds showing particular promise as extreme pressure lubricants or additives are N,N-dibutyl-9,l0- epithiostearamide, N,N-dibutyl-9,l0- l 2, l3-diepithiostearamide, 9,10-epithiostearoyl morpholine, N- ethoxyethoxyethoxypropyl-9,l0-epithiostearamide, N- 9,l0-12,13-diepithiostearoylmorpholine and N-[9(10)- hydroxy-9(10)-dibutylphosphatolstearamide, as well as epithioated soybean oil, an epithioated glyceride, 9,10-epithiostearyl '9,l0-epithiostearate and epithioated (o)oba oil both simple alkyl esters, and other ester types as 1,3-bis(9,10-epithiostearoyloxy)propane,

2-ethoxyethyl 9,10-epithiostear'ate, 2-(2-ethoxyethoxy)ethyl 9,10-epithiostearat'e, 2 -ethoxyphenyl 9,10-epithiostearate, 9,10-epithiostearyl pentachlorostearate, 4-methoxyphenyl 9-, 1 O-epithiostearate, 9,10-ep'ithiostearoyl terminated sebacic acid-1,3-propanedi0l polyester, N-methyl-N-[ 2-(9, 1 O-epithiostearoyloxy )ethyl]- 9,10-epithiostearamide, N-[2-(9,10- epithiostearoyloxy)ethyl1-9,lO-epithiostearamide, 1,3- bis epithiostearoyl imidazolidine, 1,3-bis epithiostearoyl hexahydropyrimidine.

Compounds showing particular promise as antiwear additives are N,N-dibutyl-[9(l0)-hydroxy-(9)l0- dibutylphosphato]stearamide and N,N-[9( l0) mercapto-(9)10-dibutylphosphatostearoyl]morpholine.

EXAMPLE 1 N-Methyl-N-butyloleamide (0.33 mole) of N-methyl-N-butylamine and 27 grams EXAMPLE 2 N,N-dibutyloleamide This material was prepared by the procedure of Example 1 from grams (0.33 mole) of oleoyl chloride 42.5 grams (0.33 moles of di-n-butylamine and 27 grams (0.33 mole) pyridine. Analysis of the product: Percent C, 78.94 (theory 79.25); percent H, 13.16 (theory 13.06); percent N, 3.44 (theory 3.56) confirm the preparation.

EXAMPLE 3 Ethoxyethoxyethoxy propyloleamide This material was prepared by the procedure of Example 1 from 100 grams (0.33 mole) of oleoyl chlo-- ride, 73.0grams (0.33 mole) ethoxyethoxyethoxypropylamine and 27.0 grams (0.33 mole) pyridine. Analysis of percent C, 71.84 (theory 72.04); H, 11.80

(theory 11.80), and N, 2.96 (theory 2.90) confirm the I preparation.

EXAMPLE 4 Ethoxyethoxypropyloleamlde This material was prepared by the procedure of Examplel from 100 grams (0.33 mole) of oleoyl chloride, 58.3 grams (0.33 mole) ethoxyethoxypropylamine and 27.0 grams (0.33 mole) of pyridine. Analyses of percent C, 71.45 (theory 73.80); percent H, 11.87 (theory l2.07); and percent N, 2.92 (theory 3.18) confirm the preparation.

EXAMPLE 5 Methoxyisopropyloleamide This material was prepared by the procedure of Example 1 from 100 grams (0.33 mole) of oleoyl chlo- EXAMPLE 7 Oleoylmorpholine This material was prepared by the procedure of Example 1 from 100 grams (0.33 mole) of oleoyl chloride. 28.7 grams (0.33 mole) of morpholine and 27.0

grams (0.33 mole) of pyridine.

EXAMPLE 8 N,N-dibutyloleamide This product was prepared following the exact procedure of Example2 except for the substitution of oleoyl chloride by linoleoyl chloride.

EXAMPLE 9 N,N-dibutyl-9,lO-pithiostearamide 120 grams (0.30 mole) of N,N-dibutyloleamide was epoxidized 'by the addition with stirring of 62.0 grams (0.36 mole) of meta-chloroperbenzoic acid in 630 ml of chloroform. Reaction was continued for 1 hour beyond final addition and the excess peracid destroyed by a small amount ofa 10% solution of Na SO The metachlorobenzoic acid was removed by a Nal-lCO wash, followed by water washing. The CHCl solution was then dried with anhydrous Na' SO, and the CHC1 stripped off to recover the product N,N-dibutyl-9.lepoxystearamide, oxirane content 3.45% (theory 3.91%). 100 grams (0.24 mole) of this product was added to a well stirred slurry of 55.7 g (0.75 moles) of thiourea and 89.5 g (0.72 moles) of benzoic acid in acetone. Stirring was continued for 3 hours beyond the terminal addition whereupon the benzoic acid was washed out with 38.8 g (0.36 mole) ofNa CO and the organic product extracted with hexane. The organic phase extract was dried and stripped to recover the product N,N-dibutyl-9,10-epithiostearamide containing 6.41% sulfur (theory 6.67%).

EXAMPLE 10 N-(9,10-epithiostearoyl)morphaline This product was prepared by the exact procedure described in Example 9 except for the substitution of oleoylmorpholine for the N,N-dibutyloleamide of Example 9. Analysis of product showed percent C, 71.22 (theory 69.34); percent H, 11.22 (theory 10.77); percent N, 3.66 (theory 3.68); percent S, 3.44 (theory 7.80).

EXAMPLE 1 l N,N-dibytl-9,10-9,10-l2,1 3-diepithlostearamide This product was prepared following the procedure described in Example 9 except for the replacement of the N,N-dibutyloleamide of Example 9 by N,N- dibutyllinoleamide, and a doubling of the molar ratios of all reagents. The product analyzed as follows: percent C. 69.64 (theory 68.57); percent H, 10.93 (theory 10.76; percent N, 3.10 (theory 3.07); percent S, 11.7 (theory 14.06).

EXAMPLE 12 N- Ethoxyethoxyethoxypropyl-9,l0-epithi ostearamide To 166 g of N-ethoxyethoxyethoxypropyl oleamide, Example 3,was added dropwise and with stirring 73.8 g of m-chloroperbenzoic acid in 800 ml of CHC1 The spent m-chloroperbenzoic acid was removed with 10% aqueous NaHCO and the epoxide recovered by drying and stripping off the CHC1 171 g of this epoxide was added dropwise to a slurry of 56 g thiourea in 1,000 ml of acetone and the concurrent addition of 43.4 g of glacial acetic acid and the reaction mixture stirred for 3 hours. The glacial acetic acid was neutralized with Na CO and the episulfide, N-ethoxyethoxyethoxypropyl- 9, 10-epithiostearamide, extracted with Skellysolve B and washed, dried, and stripped. lts elemental analysis was C 67.1 (66.52), H 11.42 (10.88), N 2.67 (2.87), S 2.29 (6.57).

EXAMPLE 13 N-Ethoxyethoxyethoxypropyl-9( 10)mercaptostearamide 173 g of N-ethoxyethoxyethoxypropyloleamide in CCl, was treated in the cold with a CCl, soltuion containing 60.9 g of bromine. Any unreacted bromine was removed by a thiosulfate wash. 140 g of the resulting dibromo compound was added dropwise to a well stirred solution of 72 g of Na. S- 9H- 0 in dimethy1su1foxide maintained at C. Stirring was continued at 80C for 3 hours. Water was added and the reaction product was extracted with hexane; washed, dried, and stripped. Elemental analysis of the product was C 66.3 (66.5); H 11.1 (10.9), N 2.7 (2.9), S 4.4 (6.8).

EXAMPLE l4 N,N-Dibutyl-9( l0)[ dibutylphosphono]stearamide g of N,N-dibutyloleamide, Example 2, 148 g of dibutyl phosphite, and 1.29 of benzoyl peroxide catalyst were heated at C for 3- /z hours. Additional units of 1.29 g of benzoyl peroxide was added after the first and second hours of reaction time. The excess dibutyl phosphite was then removed by distillation at reduced pressure, 0.45 mmHg. The stillpot contents showed strong adsorption bonds at 8.9.3, and 9.7 microns characteristics of the phosphonate group. The elemental analysis was C obs 71.46 (69.50), H obs 12.42 (11.92), N obs 2.20 (2.38), P obs 4.2-1 (5.28) percent respectively.

EXAMPLE 15 N9,10-12,13-diepithiostearoylmorpholine This product was prepared by the same procedure described in Example 9 except for the substitution of linoleoyl morpholine for the N,N-dibuty1oleamide of Example 8 and the doubling of molar proportions of the m-chloroperbenzoic acid in the epoxidation step and the thiourea and benzoic acid in the epithioation" step. The elemental analysis was C obs 68.89 (63.92), H =obs 10.26 (9.44), N =obs 3.29 (3.38), S obs 4.00 15.49) percent respectively.

EXAMPLE l6 N,N-Dibutyl-l 9( l0 )-hydroxy-( 9) lO-dibutylphosphatolstearamide 44.7 g of dibutylhydrogen phosphate was added to 182.2 g of N,N-dibutyl-9,lO-epoxystearamide at 90 95C with stirring. Reaction conditions were continued for 3-/2 hours after termination of the addition. The reaction product was dissolved in commercial hexane and the unreacted dibutyl hydrogen phosphate neutralized and washed out with portions of aqueous 10 NaHCO followed by several water washes. Acidulation of the hexane phase with diluted HCl followed by several water washes, drying and stripping, yielded the product. Elemental analysis was, C obs 66.56 (65.91 H obs 11.04 (11.30), N obs 2.90 (2.26). P obs 3.04 (4.20).

EXAMPLE 17 N-[ 9( 10 )mercapto-(9 1 0-dibutylphosphatostearoyl morpholine 12 g of dibutylhydrogen phosphate was added dropwise with stirring to 51.0 g of (9,10-epithiostearoyl)- morpholine, the preparation of Example 10, at 8590C and the heating and stirring continued for 3 hours beyond the terminal addition. The reaction product was dissolved in commercial hexane and any excess or unreacted was neutralized and washed out with aqueous 10% NaHC0 The hexane extract was washed several times with water dried and stripped. The elemental analysis of the product was C obs 66.74 (69.36), H obs 10.69 (11.05), N obs 2.89 (3.32), S obs 3.27 (2.17), P obs 1.68 (2.10) percent respectively.

EXAM PLE l8 9,10-Epithiostearyl 9,10-epithiostearate 140 grams of a commercial oleic acid (Emersol 233LL), 119 g of commercial oleyl alcohol (Aldol 85) and 50 ml of toluene were refluxed in the presence of 3 g of p-toluene sulfonic acid-for 24 hours, with a continual removal ofthe water of reaction by a Dean-Stark trap. The reaction mixture was freed of p-toluene sulfonic acid and any unreacted fatty acid by repeated washings with aqueous NaHCO solution. The product, oleyl oleate, was isolated by stripping off the toluene from the Na S0, dried mixture.

The oleoyl oleate was converted to 9,10-epoxystearyl 9,10-epoxystearate by treatment with a chloroform solution of meta-chloroperbenzoic acid containing 5% excess of per acid over that theoretically necessary to epoxidize the two double bonds present per mole of oleoyl oleate. The product 9,10-epoxysteary1 9,10- epoxystearate had an oxirane content of 4.99.

112 g of the 9,10-epoxysteary1 9,10-epoxystearate was converted to 9,10-epithiostearyl 9,10-epithiostearate by the dropwise addition of a l-4 dioxane solution (300 ml dioxane) of the former over a 2-2-V2 hour period to a vigorously stirred aqueous solution containing 34.2 g of thiourea in minimal water and 22.0 g of H50 as a 30% aqueous solution maintained at a temperature of 5C.

EXAMPLE l9 Epithioated Soybean Oil 300 grams of a commercially available epoxidized soybean oil (oxirane content 7.1%) was dissolved in 500 ml of 1-4 dioxane and added dropwise over a 2 hour period to a vigorously stirred solution composed of 101.2 gof thiourea in minimal water and 65.0 g of H (the latter as a 30% aqueous solution), maintained at 5C. After the addition was completed the reaction mixture was raised to 40C and kept stirred for 2 hours as it cooled. 70.6 g of Na C0 in the form of a 10% aqueous solution was added with stirring and the mixture warmed up to 40C and stirring continued for 1 hour. The epithioated soybean oil was then extracted with 200 ml of benzene and the extract washed, dried,

and the benzene stripped off. The recovered oil had a sulfur content of 6.97% as opposed to a theoretical value of 13.25% for total conversion of oxirane to thilrane.

EXAMPLE 20 Epithioated Jojoba oil g of jojoba oil (1 V 83.6) was epoxidized by the addition of 133.0 g of m-chloroperbenzoic acid in 1,500 ml of CHCl while maintaining a temperature of 20-25C to an oxirane content of 3.56%. The recovered product (131 g of epoxide) was converted to the epithio analog by its reaction with 30.9 g thiourea and 66.6 g of H S0 following the same reaction procedure described in Example 19. The reaction mixture was treated with 21.5 g of Na C0 in 195 ml of H 0 following the procedure of Example 19 and the epithio analog recovered as described in the previous example. The thiirane content (epithiosulfur) was 2.31%. Complete conversion of oxirane to thiirane should have given 6.87% sulfur.

EXAMPLE 2] 9.10-Epithiostearoyl terminated polyester of sebacic acid and 1,3-prop'ane diol.

l. g-(0.82 moles) of dimethyl sebacate was added dropwise to a refluxing mixture of 1 10 g (1.44 moles) of 1,3-propane diol and 7.0 g of sodium methoxide in an apparatus equipped with a condenser, Dean-Stark trap and short Vigreux column intervening between trap and flask. Reaction was stopped when mixture became viscous and visible evolution of methanol was no longer observed. The alkoxide catalyst was killed with dilute hydrochloric acid and the polyester dissolved in diethyl ether was washed, the solution dried and stripped. The recovered product had a molecular weight of 493 and a hydroxyl content of 5.20%.

11. 144.6 g of oleoyl chloride was added dropwise to 158 g of the product 1 in 38.0 g of pyridine and 100 m1 of benzene with vigorous stirring. The crude reaction product was filtered washed and dried and passed through two successive activated alumina columns using diethyl ether as the solvent system to remove any free acid.

111. 100 g of product 11 was epoxidized by the addition at 2025C with stirring of 34.4 g of metachloroperbenzoic acid in chloroform. The epoxide product was processed and recovered as described in previous examples. The oxirane content of the product was 2.30%.

IV. The epoxy polyester 111, 100 g, in 200 ml of dioxane was added dropwise over a 2-3 hour period to 6.4 g of thiourea in minimal water to which had been added 4.2 g of H S as a 30% aqueous solution. The addition was carried out with vigorous stirring with the temperature maintained at +C. After the addition was complete the reaction mixture was warmed up to 40C and stirred for l-2 hours and allowed to cool and 4.7 g of Na C0 in 50 ml of water added, the mixture again warmed up to 40C with stirring. The product was then extracted with benzene, washed dried and stripped. Analysis showed a sulfur content of 1.1%.

EXAMPLE 22 l. N-[2-(9,10-epithiostearoyloxy)ethyl]-9,IO-epithiostearamide. 150 g of oleoylchloride was added dropwise with stirring to 15.2 g of ethanolamine and 19.7 g of pyridine in 300 ml of benzene. The product N-(2-o1eoy1oxyethyl)oleamide was recovered in the v usual manner.

11. The product 1, 100 g, was epoxidized as described in preceeding examples with 69.0 g of metachloroperbenzoic acid. The epoxide N-[2-(9,10- epoxystearoyloxy)ethyl]-9, l0-epoxystearamide was produced in about a 50% yield. It had an oxirane content of 3.50%.

111. 112 g of the diepoxide 11 was added dropwise to a well stirred mixture of 59.6 g of thiourea and 95.6 g of benzoic acid in 500 ml of acetone at room temperature. After stirring for a total of 3 hours it was treated with 55.0 g of K C0 in 600 ml of water. The product was extracted with Skelly B washed, dried, and stripped. The product whose principal component was N-[2-(9,lO-epithiostearoyloxy)ethyl]-9, IO-epithiostearamide gave the following analysis: C=69.24 (69.83), H 10.66 (10.87), N 1.97 (2.14), S =6.50 (9.80). Calculated value in parentheses.

EXAMPLE 23 N-Methyl-N-[2-(9,lO-epithiostearoyloxy)ethyl]- 9,10-epithiostearamide.

l. 300 g of oleoyl chloride was added with stirring to 38.5 g of N-methylethanolamine and 39.5 g of pyridine in 200 ml of benzene. The product N-methyl-N-(2- oleoyloxyethyl)oleamide was recovered in the usual manner.

11. 125 g ofl was epoxidized by the addition of 84.3 g of meta-chloroperbenzoic acid at 20-25C in CHCI The recovery and isolation and procedures were the same as described in preceeding examples. The product composed principally of N-methyl-N-[2-(9,l0 epoxystearoyloxy)ethyl]-9, IO-epoxystearamide had an oxirane content of 4.74%.

111. 100 g of 11 was added dropwise over a 2-3 hour period to a slurry of 52 g of thiourea and 82.9 g of benzoic acid in 700 ml of acetone at room temperature. 200 ml of Na C0 was then added and the epithio compound recovered as in the preceeding example. The product N-Methyl-N-l2-(9,l0- epithiostearoyloxy)ethyl]-9,IO-epithiostearamide. Elemental analysis. calculated values in parentheses was as follows: C 70.53 (70.19), H 10.59 (10.94), N 2.75 (2.10), S 5.50 (9.59).

EXAMPLE 24 0 4-Methoxyphenyl 9, l O-epithiostearate.

A. 4-Methoxyphenyl oleate This product is prepared using 27.3 g (0.22 mole) of 4-methoxyphenol, 17.4 g (0.22 mole) of pyridine dissolved in 150 m1 of benzene, and 66 g (0.22 mole) of oleoyl chloride which is added dropwise with stirring. After stirring for an additionalhour the mixture is filtered, washed successively with dilute hydrochloric acid and water, and dried over anhydrous sodium sulfate. Free acid is re- .moved by percolating the benzene solution through a column of activated alumina. The solvent is then removed by stripping under reduced pressure.

B. 4-Methoxyphenyl 9,10-epoxystearate 31.2 g (0.18 mole) of meta chloroperbenzoic acid was dissolved in 400 m1 of chloroform and added slowly to a solution containing 61 g (0.16 mole) of A and 150 m1 of chloroform. After stirring for an additional hour, the excess m-chloroperbenzoic acid was destroyed using a 10% solution of sodium sulfite, after which mchlorobenzoic acid was neutralized-with Na- C0 and the solution washed with water, dried over anhydrous Na S0 filtered and stripped.

C. 4-Methoxyphenyl 9,10-epithiostearate 11.9 g (.16 mole) thiourea in 60 ml of water was added to 7.9 g (.08 mole) of sulfuric acid in 40 ml of water. The mixture was cooled to 5C after which 63 g (0.16 mole) of 4-methoxyphenyl 9,10-epoxystearate which was dissolved in 150 ml of dioxane was added to the mixture with stirring over a two-hour period, the temperature being maintained at 5C. After the addition, the mixture was heated to 40C, the heat removed and then stirred for two hours. The mixture was neutralized with 8.5 g (.08 mole) of anhydrous sodium carbonate in 100 ml of water and warmed to 40C. The heat was removed and the reaction continued for one hour. The mixture was extracted with 3-50 ml portions of diethyl ether, after which the ether extract was washed with water until neutral, dried over anhydrous sodium sulfate and stripped. S 4.79 (7.61

EXAMPLE 25 2-(2-Ethoxyethoxy)ethyl 9,10-epithiostearate.

EXAMPLE 26 2-Ethoxyethyl 9,1 O-epithiostearate.

This product was prepared as described in Example 24 from 18.5 g (0.24 mole) of thiourea, 11.8 g (0.12 mole) of sulfuric acid and g (0.24 mole) of 2- ethoxyethyl-9,l0 epoxystearate. S 5.74, (8.28).

EXAMPLE 27 2-Ethoxypheny1 9,10-epithiostearate. This product was prepared as described in Example 24 from 19.3 g (0.25 mole) of thiourea, 12.3 g (0.13

mole) of sulfuric acid, and 106 g (0.25 mole) of 2- ethoxyphenyl-9.lO-epoxystearate. S 5.1 (7.36).

9 EXAMPLE 2s l,3-Bis(9, l O-Epithiostearoyl )imidazolidine A. N,N'-Ethylenebisoleamide This product was prepared by adding with stirring 200 g (0.66 moles) of oleoyl chloride to 19.9 g (0.33 mole) of ethylenediamine in the presence of 52.6 g (0.66 mole) of pyridine using benzene as a solvent. After filtration employing a Buchner funnel, the filtrate was washed with dilute hydrochloric acid, followed by water. then was dried over anhydrous sodium sulfate, filtered and stripped. N,N'-ethylene bis oleamide was recrystallized twice from acetone.

B. l,3-Dioleoylimidazolidine 1,3- 1.)ioleoy1imida'/.o1idine was prepared from 71.5 g (0.12 mole) of N,N'-ethylenebisoleamide and 21.8 g formaldehyde solution (36.8%) in 150 ml of acetic acid containing a catalytic amount (4 ml) of 37% hydrochloric acid. Those materials were placed in a flask and stirred by means of a magnetic stirring bar while the temperature was raised to 50C and held at this temperature for 2 hours. Then the acetic acid, excess formaldehyde solution and hydrochloric acid were removed by distillation at reduced pressure. The product was recrystallized twice from absolute ethyl alcohol and dried in a vacuum desiccator over phosphorus pentoxide.

C. l,3-Bis(9,l-epoxystearoyl)imidazolidine This product was prepared as described in Example 24 from EXAMPLE The compounds prepared in accordance to the proccdures given in Examples 1 through 29 were evaluated as base lubricants in the Shell Four-Ball Wear tests following a modified procedure of ASTM D2266-67. The resulting scar diameter on the balls after running at 600 rpm for 1 hour at 120C and Kg load were compared with the scars obtained using commercial lubricants such as Aeroshell Mil-L-708 (Di-2-ethylhexyl sebacate and additive), Gulfpride, single G, MS, multiviscosity.'

and sec. paraffin oil. The results of these tests are reported in Table l and Table 1A A.

TABLE 1 ANTlWEAR LUBRICANT PROPERTIES OF FATTY ACID AMlDES Avg. Wear Scar. mm

COMPOUND without with 5 7,

, additive additive Additive 1. N.N-Bis( 2-ethoxy- N.N-Di-butyl-9. l0-epiethyl)oleamide 0.597 0.735 thiostearamide 2. N,N-Di-n-buty1-9,10-

epithiostearamide 0.842 none 3. Oleoylmorpholine 0.623 0.658

4. N,N-Dimethyloleamide 0.797 0.987

5. N,N-Di-n-propyloleamide 0.908 0.885

6. N,N-Di-n-hcxyloleamidc 0.893 0.898 7. N,l 1-Di-n-butylerucamide 0.758 0.798

8. N,N-Di-n-butyl amide of Se]. hydrogenated cottonseed fatty acids 0.798 0.958

9. N.N-Bis( 2-Mcthoxyethy1)o1eamide 0.626 0.725

10. N.N-Dihutyloleamidc 0.710

l l. N-Olcoyl-4-propylpipcridine 0.847

12. Morpholiclc of sel.

hydrogenated cottonseed fatty acids ().642

l3. N-Mcthyl-N-butylolcamide 0.607

14. N-Ethoxyethoxyethoxypropyoleamide 0.503

15. N-Ethoxyethoxypropyloleamide 0.526

t 16. N-Methoxyisopropylolcamidc It can be seen from the data presented that the N- alkoxyalkyl and N,N-di(alkoxyalkyl)oleamides, without the assistance of additives, exhibited wear characteristics (i.e., low scar diameters) comparable to the commercial controls Aeroshell and Gulfpride which do contain additives to improve performance. N,N- dibutyl-[ 9( l0 )-hydroxy-( 9 IO-dibutylphosphato stearamide and N-[9( l0 )mercapto-(9) l0- dibutylphosphatostearoyl]morpholine not only' exhibit low wear characteristics in themselves. but also impart as additives such characteristics to paraffin oil and DOS base lubricants. A large number of these, particularly the esters and ester amides such as PC-O-7857, 7858, 7859, 7887,7953, 7954, 7955, 7956, 7958, and 7959, although poor in wear characteristics as base oils, are very effective anti-wear additives for either,

paraffinic or diester base oils, in some instances both.

EXAMPLE 31 The various amides were evaluated as extreme pressure lubricants or additives in a Shell 4-ball extreme pressure tester at 1,440 PPM following ASTM Procedure D 2596-67T. Loads were increased in increments TABLE II EXTREME PRESSURE TESTS (ASTM D2506-o7T) Weld Point Weld Point COMPOUND (No (with 591 additive) No. 2)

l -N,N-Bis( 2-ethoxyethyl) 120 I70 oleamide 2 N,N-Din-butyl-9,lO-epithi- 300 osteara mide 3. Oleoylmorpholine I20 I50 4. N .N-Dimethyloieamide 120 l 40 5. N,N-Di-n-propyloleamide I20 I50 6. N,N-Di-n-hexyloleamide 120 180 7. N,N-Di-n-butylerucamide l 20 200 8. N,N-Di-n-butyl amide of I20 I70 hydrogenated cottonseed fatty acids 9. N,N-Bis(2-Methoxyethyl- 120 I60 )oleamide l0. N-Methyl-N-butyloleamide 100 l 1. N.N-Dibutyl-9,lO-epithios- 300" tearamide.

l2. N.N-Dibutyl-9.l0-l2.l3- 440 diepithiostearamide l3. -N-Ethoxyethoxyethoxy- 120 propyoleamidc l4. N-Ethoxyethoxypropyloleu- 120 mitle l5. N- ltlil Methoxyisopropyloleamide l6. N-Methoxyethyloleamide I00 17. N-9. l O-epithiostearoylmor- 380 pholine TABLE ll-Continued EXTREME PRESSURE TESTS (ASTM D2506-67TJ EVALUATION OF N.N-DlBU'l'YL-9,l0-l2.lJ-DI-EPITHIOSTEARAMIDE AS AN ADDITIVE AND AS A BASE Oll. lN EXTREME PRESSURE TESTS. (ASTM D2596-(17T) BASE OIL "/1 LOAD. Kg WEAR SCAR ADDlTlVE mm I00 sec Parafi'm Oil (5%) l4() 1.90 200 2.35 220 2.75 240 Weld- 5 sec.

BislZ-ethylhexyl (S /1) I20 l .5 l

sebacate lBO 1.59 I (T.S.)" 2.47 200 Weld- 4 sec. (I071) 240 2.88 260 3.55 270 Weldl0 sec.

N,N-Dihutyl-9,l0- None l2() L38 l2,l 3-diephithios-' tearamide I60 l.ol 200 L89 280 ll 320 247 360 2.70 400 2.88 440 \Vcltl- 6 Set.

"Incipient seizure EXTREME PRESSURE TESTS ON N-ETHOXYETHOXYETHOXYPROPYL- ).l0-EPlTHlOSTEARA- MlDE (PC-O-No. 7682) ADDITIVE APPLIED LOAD AYE. SCAR BASE OIL None Iv n

EVALUATION OF ETHOXYETHOXYETHOXYPROPYL PENTACHLOROSTEARAMIDE (POO-7857) AS AN ADDITIVE lN EXTREME PRESSURE TESTS TABLE III-Continued EVALUATION OF N-METHYL-N-l 2-(9. lO-EPITHIOSTEAROYLOXY )ETHYL1-9. l EPITHIOSTEARAMIDE (PC-07858) AS AN ADDITIVE AND A BASE OIL IN EXTREME PRESSURE TESTS Additive Base Oil Load, Kg Wear Scar. mm

POO-7858 none 120 0.833

" 200 L7! 260 2.08 300 1.88 360 2.37 420 2.42 460 2.57 480 3.15 490 Weld 3 sec.

D.O.S. PC-O-7858 120 2.55 140 2.95 200 3.43 21.0 3.52 220 Weld 20 sec.

S105 Topaz Oil POO-7858 I20 2.65 I60 3.28 I80 3.32 I90 Weld 17 see.

5105 Topaz Oil none 120 Weld sec.

I02 sec Paraffin Oil 7682 (5%) 120 2.28 140 2.46 150 weld D.O.S. 7682 (5%) I 2.23 H 140 2.44 I50 weld EXTREME PRESSURE TESTS 0N N-ETHOXYETHOXYETHOXYPROPYL-9( IOLMERCAPTOS- TEARAMIDE (POO-7683) BASE OIL ADDITIVE APPLIED AVE. SCAR.

LOAD, Kg mm 7683 None 200 1.54

I02 sec Paraffin Oil 7683 (5%) 120 L97 140 2.35

" I60 weld D.O.S. 7683 (57:) I20 L68 I40 2.18

" I80 weld Test stopped because of extreme decomposition. Did not weld.

EXTREME PRESSURE TESTS ON N-(9.l0-l2.l3-DIEPITHIOSTEAROYLIMORPHOLINE (PC-O-No.

TABLE III-Continued EXTREME PRESSURETESTS ON N-(9.10-l2. l3-DIEPITHIOSTEAROYLIMQRPHOLINE l O Test stopped because of extreme decomposition. Did not weld.

EXTREME PRESSURE TESTS ON N.N-DIBUTYL-9( l())-( DIBUTYLPHOSPHONO)STEARAMIDE (PC-(I-No. 7685) APPLIED LOAD AVE. SCAR, BASE OIL ADDITIVE Kg mm 5 7685 None 120 3.115 I40 4.50 I50 weld EXTREME PRESSURE TESTS ON N,NDIBUTYL-I9( I 0)-HYDROXY-9( IOI-DIBUTYLPHOS- 20 PHATOISTEARAMIDE (PC-O-No. 7686) 7686 None 200 0.887

" 300 2.78 340 4.32 350 4.50 360 weld I00 sec Paraffin Oil 7686 (571) I20 2.28 I40 2.80 I50 3.0l I60 .weld

D.O.S. 7686 15 /11 120 1.95 I 2.85 I 3.03 I weld EXTREME PRESSURE TESTS ON N-[9( l0)-MERCAPTO-9( l0)-DIBUTYLPHOSPHATOS- 35 TEAROYLIMORPHOLINE (OC-O-No 7687) APPLIED AYE. SCAR.

LOAD BASE OIL ADDITIVE Kg mm 7687 None I20 0.608

I60 L 35 40 200 L40 240 L 280 3.36

EXTREME PRESSURE TESTS ON N,N-DIBUTYL-9( I0)-CARBOBUTYOXYOCATDECANAMIDE (PC-O-No. 7688) 45 7688 None L92 )0 2. I S I00 2.45 I20 weld Test stopped because of extreme decomposition and noxious fumesv 50- Did not weld.

EVALUATION OF N-[2-(9.lO-EPITHIOSTEAROYLOXY)ETHYLI").III-EPITHIOS- -TEARAMDIE (POO-7859) AS AN ADDITIVE AND A BASE OIL IN EXTREME PRESSURE TESTS TABLE III-Continued EVALUATION OF ETHOXYETHOXYETHOXYPROPYL-9. l I 2.I 3-DIEPITHIOS- TEARAMDIE (PC-0-786l) AS AN ADDITIVE AND A BASE OIL IN EXTREME PRESSURE TESTS "No weld point; very little decomposition.

EVALUATION OF N-METHYL-N-PHENYL-9,lO-EPITHIOSTEARAMIDE (PC-0-787I) AS AN ADDITIVE AND AS A BASE OIL IN EXTREME PRESSURE TESTS EVALUATION OF I ,3-BIS(9. I O-EPITHIOSTEAROYLOXY )PROPANE (POO-7863) AS AN ADDITIVE AND A BASE OIL IN EXTREME PRESSURE TESTS Base Oil Additive Load. kg Wear Scar, mm

PCO-7863 none I20 0.90 200 I.2I 300 2.23 340 3.42" 360 2.85" 380 3.17" 390 3.47" 400 Weld 2 sec.

D.O.S. PCO-7863 I20 2.49 140 2.65 I60 2.78 I80 3.18 I90 Weld 8 see.

8105 Topaz Oil PCO-7863 I20 2.37 140 2.67 I50 2.72 I70 Weld 10sec.

S105 Topaz Oil none I20 Weld l5 sec.

"Some Corrosion TABLE III-Continued EVALUATION OF I ,3-DI(9, I O-EPITI-IIOSTEAROYL)HEXAHYDROPYRIMIDIN E (PCO-7887) AS AN ADDITIVE AND A BASE'OIL IN EXTREME PRESSURE TESTS Base Oil Additive Load. Kg Wear Scar. mm

PCO-7887 none I20 0.782

" 320 Weld 30 sec.

D.O.S. PCO-7887 I20 2.30 I40 2.48 I60 2.74 I70 2.89

I80 Weld l0 sec.

S105 Topaz Oil PC-0-7887 I 2.81 I30 2.94 I40 Weld 15 sec.

, SI05 Topaz Oil none I20 Weld l5 sec.

EVALUATIONN OF Z-ETHOXYETHYL 9,10-EPITHIOSTEARATE (POO-7953 )'AS AN ADDITIVE IN EXTREME PRESSURE TESTS Base Oil Additive,5/z Load. kg WcurSczir. mm

D.O.S. P007953 120 I I 3 160 2.65 200 2.97 240 2.99 250 Weld 7 sec.

Topaz S105 Oil PCO-7953 I20 ".47 I50 2.68

" I60 Weld -I set.

EVALUATION OF Z-(Z-ETHOXYETHOXY )ETHYI. 9,10-EPITHIOSTEARATE (POO-7954) AS AN ADDITIYE IN EXTREME PRESSURE TESTS Base Oil Additive,5'/ Loud. kg Wear Scar. mm

D.O.S. PCO-7954 120 0.885

" I60 272 I70 Weld 9 sec.

40 Topaz S105 Oil POO-7954 I20 2.45 I40 3. l7 I50 Weld 10sec.

EVALUATION OF Z-ETHOXYPHENYL JJO-EPITHIOSTEARATE (PCO-7955) AS AN ADDITIVE IN EXTREME PRESSURE TESTS Base Oil Additive. 5% Load. kg Wear Scar. mm

D.O.S. PCO-7955 I20 0.863

" 160 2.62 I70 Weld 7 sec.

Topaz S I05 Oil PCO-7955 120 2.24 I40 2.51 I50 2.75 160 Weld 6 sec.

5 EVALUATION OF @METHOXYPHENYL QJO-EPITHIOSTEARA'IE (PCO-7956) AS AN ADDITIVE IN EXTREME PRESSURE TESTS Base Oil Additive. 5'71 Loud, kg Wear Sour. mm

D.O.S. POO-7956 120 0.963

" 200 Weld h we Topaz Sl05 Oil P007956 I30 2.38 I40 2.37 I80 2. 200 3.78 2m Wold q 4 sec.

TABLE Ill-Continued 22 TABLE Iii-Continued EVALUATION OF l,3-BlS-(9. I O-EPITHIOSTEAROYL)-IMIDAZOLIDINE (PCO-7957) AS AN ADDITIVE lN EXTREME PRESSURE TESTS Base Additive, Load kg w scar mm Base Oil Additive. 5% Load, kg Went Scar. mm D.O.S. PC-0-7957 120 1.42 9- :gg 150 0.897 180 3'1; I, 5 1 23 H 200 0 .0 I, H

8 Topaz 5105 011 Poo-7961 120 2.40 n n 7 Topaz $105 011 PC-0-7957 120 0.855 {3g 160 1.01 .1 ,1 7, 200 "09 I90 Weld 7 set. 260 1.17 280 2.68 l5 290 Weld 8 sec.

EVALUATION OF EP1T1-110ATED SOYBEAN 01L (PCO-7958) As AN ADDlTlVE AND As A BASISE 21L 1N EXTREME PRESSURE TE T Base 011 Additive. 5% Load, kg Wear Scar. mm TABLE V "99 8 1 EVALUATION OF N-QJO-EPITHIOSTEAROYLQ MORPHOLINE 260 As AN ADDlTlVE AND As A B SE 011. IN EXTREME 320 PRESSURE TESTS (ASTM D 2s9s-e7'r1 I: If $8,, 25 A 77 LOAD wEAR scAR 4 BASE OiL ADDITIVE Kg mm 9 P0057958 I 100 sec Paraffin 011 (5'71) 120 2.011 150 1.03 M0 8U 200 1.1.5 I60 260 1.77 I, 1, 280 2.70 l8) weld. l0 sec 29o 2.78 v g 1. 1. 300 weld 3 sea B1s(ee)t;1cyz1:xyl) (5:71) 82% 5.6;!

' I! I! Topaz S105 011 P0057958 120 2.23 :3: I: :38 52 1110 1.1111

. I, ,1 200 weld 9 sea I -00 veld set.

. N-9,l0-Epithio- "T est stopped because o f ha rsh fumes and decomposltlon. stearoylmorpholine None I20 0.70

- 200 2.13 240 1,43 EVALUATION OF 9,IO-EPITHIOSTEARYL 300 9.10-EP1TH10sTEARATE (PCO-7959) As AN ADDITIVE AND As 380 WM 50 m A BASE 011. IN EXTREME PRESSURE TESTS 40 Base Oil Additive. 5% Load, kg Wear Scar. mm

Poo-7959 none. 120 1.40 I60 1.74 200 1.75 300 3.77 310 Weld 9 sec. we claim: V D.0.S. Pee-7959 120 1.90 l. A compositiop of matter useful as a base lubricantff $88 with low wear characteristics consisting of a paraffin 240 1 base oil and an anti-wear additive selected from the I" Z" 290 2.89 group consisting of N-methyl-N-[2-( 9,10- 300 3 epithiostearoyloxy)-ethyl19,lO-epithiostearamide, N- Topaz 5105 on 0 959 0 7 [2:(9.lo epithiosteareyloxy)ethyll-9, l O-cpithiosteara $38 is? mlde, l.3-d 9.l Pithiostear0yl)hexahydro- H H 240 pyrimidine, 2-ethoxyethyl 9.1 Q-epithiostearate. I: If 2 2-(2-ethoxyethoxy)ethyl 9.l0-ep1th1ostearate. 1.3-b1s- 8 (9.l0epithiostearoyl)imidazolidine and epithioated o o 9 10 EPITHIO STEARYL soybean I EVALUATI N F PENTACHLOROSTEARATE (PCO-7960) As AN AtmlTlvE 1N T "fumposmon of 1 l the EX RE PRESSURE 'rEsTs addit ve 1s N-methyl-N-[-- (9.l0-ep1th1ostearoyl0xy Base Oil Additive,5% Loud, kg Wear Scar. mm ethy|].Q l (Lepithiostearamide DDS PGMQGO '20 L87 3 fhe composmon of clm l wherem the amt-wear 150 1.78 addttlve 1s N-[2-(9.l0-ep1th1ostearoyloxy)ethyl1-9.l0- epithiostearamide 0 1 s Wed 4. The composmon of cla1m l wherem the arm-wear Topaz S Oil PCO-7860 65 additive is l,3-di(9.lO-epithiostearoyl)hexahydro- I50 L16 m-d 200 1.39 1 P l I I 220 2.67 5. The compos tion of claim 1 wherem the amt-wear 230 Weld 4 sec.

EVALUATION OF 9,!0-EPITHIOSTEAROYL TERMINATED SEBACIC ACID-IJ-PROPANEDIOL POLYESTER (POO-7961 AS AN ADDlTlVE IN EXTREME PRESSURE TESTS additive is Z-e'thexyethyl 9.10-epithiostearate.

6. The composition of claim 1 wherein the anti-wear additive is 2-(2-ethoxyethoxy)ethyl 9,10-epithiostearate.

7. The composition of claim 1 wherein the anti-wear additive is epithioated soybean oil.

8. The composition of claim 1 wherein the anti-wear additive is l ,3-bis-(9, l O-epithiostearoyl)imidazolidine.

9. A composition of matter useful as a base lubricant with low wear characteristics consisting of a diester base oil and an anti-wear additive selected from the group consisting of N-[ 2-(9, lepithiostearoyloxy )ethyl1-9, 1 O-epithiostearamide, 2- ethoxyethyl 9,10-epithiostearate, 2-(2-ethoxyethoxy)ethyl 9,10-epithiostearate, 2-ethoxyphenyl 9,10-epithiostearate, and 9,l0-epithiostearyl 9,10-epithiostearate.

10. The composition of claim 9 wherein the anti-wear additive is N-[2-(9,10-epithiostearoyloxy)ethyl]-9,l0- epithiostearamide.

11. The composition of claim 9 wherein the anti-wear additive is 2-ethoxyethyl 9,10-epithiostearate.

. 12. The composition of claim 9 wherein the anti-wear additive is 2-(2-ethoxyethoxy)ethyl 9,10-epithiostearate.

13. The composition of claim 9 wherein the anti-wear additive is Z-ethoxyphenyl 9,l0-epithiostearate.

14. The composition of claim 9 wherein the anti-wear additive is 9, lO-epithiostearyl 9,10-epithiostearate.

15. An extreme pressure lubricant composition wherein the base lubricant is a paraffin base oil and the extreme pressure additive is selected from the group consisting of N-methyl-N-[ 2-( 9, l 0- epithiostearoyloxy)ethyl]-9,IO-epithiostearamide, N- [2-(9, lO-epithiostearoyloxy)ethyl]-9,10-epithiostrearamide, l,3-bis(9,lO-epithiostearoyloxy)propane, 2-ethoxyethyl 9,l0-epithiostearate, 2-(2-ethoxyethoxy)ethyl 9,lO-epithiostearate, 2-ethoxyphenyl 9,10-epithiostearate, 4-methoxyphenyl 9,10-epithi0stearate, 1,3 -bis( 9, l O-epithiostearoyl )-imidazolidine, epithioated soybean oil, 9,10-epithiostearyl 9,1 O-epithiostearate, 9,10-epithiostearyl pentachlorostearate, and 9,10-epithiostearoyl terminated sebacic acid-1,3- propanediol polyester.

16. The composition of claim wherein the extreme pressure additive is N-methyl-N- 2-( 9, l 0- epithiostearoyloxy )ethyl)-9, l O-epithiostearamide.

17. The composition of claim 15 wherein the extreme pressure additive is N-[2-(9,l0- epithiostearoyloxy )ethyl] -9, IO-epithioste aramide.

18. The composition of claim 15 wherein the extreme pressure additive is l,3-bis(9,l0-epithiostearoyloxy)- propane.

19. The composition of claim 15 wherein the extreme pressure additive is 2-ethoxyethyl 9,10-epithiostearate.

20. The composition of claim 15 wherein the extreme pressure additive is 2-(2-ethoxyethoxy)ethyl 9,10-epithiostearate.

21. The composition of claim 15 wherein the extreme pressure additive is 2-ethoxyphenyl 9,10-epithiostearate.

'22. The composition of claim 15 wherein the extreme pressure additive is 4-methoxyphenyl 9,10-epithiostearate.

23. The composition of claim 15 wherein the extreme pressure additive is l,3-bis(9,l0-epithiostearoyl)- imidazolidine.

24. The composition of claim 15 wherein the extreme pressure additive is epithioated soybean oil.

25. The composition of claim 15 wherein the extreme pressure additive is 9,10-epithiostearyl 9,10-epithiostearate.

26. The composition of claim 15 wherein the extreme pressure additive is 9,10-epithiostearyl pentachloros- 29. The composition of claim 28 wherein the extreme pressure component is N-methyl-N-[2-(9, l0- epithiostearoyloxy)ethyl1-9, l O-epithiostearamide.

30. The composition of claim 28 wherein pressure component is N-[ 2-( 9 l O- epithiostearoyloxy)ethyl]-9,lO-epithiostearamide.

31. The composition of claim 28 wherein the extreme pressure component is l ,3-bis(9, IO-epithiostearoyloxy)propane.

32. The composition of claim 28 wherein the extreme pressure component is l,3-di(9,lO-epithiostearoyl)- hexahydropyrimidine.

33. The composition of claim 28 wherein the extreme pressure component is 2-ethoxyethyl 9,10-epithiostearate.

34. The composition of claim 28 wherein the extreme pressure component is 2-(2-ethoxyethoxy)ethyl 9,10-epithiostearate.

35. The composition of claim 28 wherein the extreme pressure component is 2-ethoxyphenyl 9,l0-epithiostearate.

36. The composition of claim 28 wherein the extreme pressure component is 4-methoxyphenyl 9,10-epithiostearate.

37. The composition of claim 28 wherein the extreme pressure component is l,3-bis(9,lO-epithiostearoyl)- imidazolidine.

38. The composition of claim 28 wherein the extreme pressure component is-epithioated soybean oil.

39. The composition of claim 28 wherein the extreme pressure component is 9,lO-epithiostearyl 9,10-epithiostearate.

40. The composition of claim 28 wherein the extreme pressure component is 9,10-epithiostearyl pentachlorostearate.

41. The composition of claim 28 wherein the extreme pressure component is 9,10-epithiostearoyl terminated sebacic acid-1,3-propanediol polyester.

is selected from the group the extreme UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION PATENT NO. 3,873,457

DATED March 25, 1975 INVENTOR(S) 1 Frank C. Magne, Robert R. Mod, Gene Sumrell and Winfred E. Parker It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

[75] Inventors: Frank C. Magne; Robert R. Mod;

Gene Sumrell, all of New Orleans, La. and Winfred E. Parker, of Philadelphia, Pa.

Signed and Sealed this twent -sec0nd [SEAL] y D 0f June1976 Arrest:

RUTH C. MASON Arresting Officer 

1. A COMPOSITION OF MATTER USEFUL AS A BASE LUBRICANT WITH LOW WATER CHARACTERISTICS CONSISTING OF A PARAFFIN BASE OIL AND AN ANTI-WEAR ADDITIVE SELECTED FROM THE GROUP CONSISTING OF N-METHYL-N-(2-(9,10-EPITHIOSTEAROYLOXY)-ETHYL)9,10EPITHIOSTEARAMIDE, N-(2-(9,10-EPITHIOSTEAROYLOXY)ETHYL)9,10-EPITHIOSTEARAMIDE 1,3-DI(9,10EPITHIOSTEAROYL)HEXAHYDRO-PYRIMIDINE, 2-ETHOXYETHYL 9,10EPITHIOSTEARATE, 2-(2-ETHOXYETHOXY)ETHYL 9,10-EPITHIOSTERATE, 1,3-BIS-(9,10-EPITHIOSTEAROYL)IMIDAZOLIDINE AND EPITHIOATED SOYBEAN OIL.
 2. The composition of claim 1 wherein the anti-wear additive is N-methyl-N-(2-(9,10-epithiostearoyloxy)-ethyl)-9,10-epithiostearamide.
 3. The composition of claim 1 wherein the anti-wear additive is N-(2-(9,10-epithiostearoyloxy)ethyl)-9,10-epithiostearamide.
 4. The composition of claim 1 wherein the anti-wear additive is 1,3-di(9,10-epithiostearoyl)hexahydro-pyrimidine.
 5. The composition of claim 1 wherein the anti-wear additive is 2-ethoxyethyl 9,10-epithiostearate.
 6. The composition of claim 1 wherein the anti-wear additive is 2-(2-ethoxyethoxy)ethyl 9,10-epithiostearate.
 7. The composition of claim 1 wherein the anti-wear additive is epithioated soybean oil.
 8. The composition of claim 1 wherein the anti-wear additive is 1,3-bis-(9,10-epithiostearoyl)imidazolidine.
 9. A composition of matter useful as a base lubricant with low wear characteristics consisting of a diester base oil and an anti-wear additive selected from the group consisting of N-(2-(9, 10-epithiostearoyloxy)ethyl)-9,10-epithiostearamide, 2-ethoxyethyl 9,10-epithiostearate, 2-(2-ethoxyethoxy)ethyl 9,10-epithiostearate, 2-ethoxyphenyl 9,10-epithiostearate, and 9,10-epithiostearyl 9,10-epithiostearate.
 10. The composition of claim 9 wherein the anti-wear additive is N-(2-(9,10-epithiostearoyloxy)ethyl)-9,10-epithiostearamide.
 11. The composition of claim 9 wherein the anti-wear additive is 2-ethoxyethyl 9,10-epithiostearate.
 12. The composition of claim 9 wherein the anti-wear additive is 2-(2-ethoxyethoxy)ethyl 9,10-epithiostearate.
 13. The composition of claim 9 wherein the anti-wear additive is 2-ethoxyphenyl 9,10-epithiostearate.
 14. The composition of claim 9 wherein the anti-wear additive is 9,10-epithiostearyl 9,10-epithiostearate.
 15. An extreme pressure lubricant composition wherein the base lubricant is a paraffin base oil and the extreme pressure additive is selected from the group consisting of N-methyl-N-(2-(9,10-epithiostearoyloxy)ethyl)-9,10-epithiostearamide, N-(2-(9, 10-epithiostearoyloxy)ethyl)-9,10-epithiostrearamide, 1,3-bis(9, 10-epithiostearoyloxy)propane, 2-ethoxyethyl 9,10-epithiostearate, 2-(2-ethoxyethoxy)ethyl 9,10-epithiostearate, 2-ethoxyphenyl 9,10-epithiostearate, 4-methoxyphenyl 9,10-epithiostearate, 1,3-bis(9,10-epithiostearoyl)-imidazolidine, epithioated soybean oil, 9,10-epithiostearyl 9,10-epithiostearate, 9,10-epithiostearyl pentachlorostearate, and 9, 10-epithiostearoyl terminated sebacic acid-1,3-propanediol polyester.
 16. The composition of claim 15 wherein the extreme pressure additive is N-methyl-N-(2-(9,10-epithiostearoyloxy)ethyl)-9,10-epithiostearamide.
 17. The composition of claim 15 wherein the extreme pressure additive is N-(2-(9,10-epithiostearoyloxy)ethyl)-9,10-epithiostearamide.
 18. The composition of claim 15 wherein the extreme pressure additive is 1,3-bis(9,10-epithiostearoyloxy)propane.
 19. The composition of claim 15 wherein the extreme pressure additive is 2-ethoxyethyl 9,10-epithiostearate.
 20. The composition of claim 15 wherein the extreme pressure additive is 2-(2-ethoxyethoxy)ethyl 9,10-epithiostearate.
 21. The composition of claim 15 wherein the extreme pressure additive is 2-ethoxyphenyl 9,10-epithiostearate.
 22. The composition of claim 15 wherein the extreme pressure additive is 4-methoxyphenyl 9,10-epithiostearate.
 23. The composition of claim 15 wherein the extreme pressure additive is 1,3-bis(9,10-epithiostearoyl)-imidazolidine.
 24. The composItion of claim 15 wherein the extreme pressure additive is epithioated soybean oil.
 25. The composition of claim 15 wherein the extreme pressure additive is 9,10-epithiostearyl 9,10-epithiostearate.
 26. The composition of claim 15 wherein the extreme pressure additive is 9,10-epithiostearyl pentachlorostearate.
 27. The composition of claim 15 wherein the extreme pressure additive is 9,10-epithiostearoyl terminated sebacic acid-1,3-propanediol polyester.
 28. An extreme pressure lubricant composition wherein the base lubricant is a diester-base oil and the extreme pressure additive is selected from the group consisting of N-methyl-N-(2-(9,10-epithiostearoyloxy)ethyl)-9,10-epithiostearamide, N-(2-(9,10-epithiostearoyloxy)ethyl)-9,10-epithiostearamide, 1,3-bis(9,10-epithiostearoyloxy)propane, 1,3-di(9,10-epithiostearoyl) hexahydropyrimidine, 2-ethoxyethyl 9,10-epithiostearate, 2-(2-ethoxyethoxy)ethyl 9,10-epithiostearate, 2-ethoxyphenyl 9,10-epithiostearate, 4-methoxyphenyl 9,10-epithiostearate, 1,3-bis(9, 10-epithiostearoyl)-imidazolidine, epithioated soybean oil, 9,10-epithiostearyl 9,10-epithiostearate, 9,10-epithiostearyl pentachlorostearate, and 9,10-epithiostearoyl terminated sebacid acid-1,3-propanediol polyester.
 29. The composition of claim 28 wherein the extreme pressure component is N-methyl-N-(2-(9,10-epithiostearoyloxy)ethyl)-9,10-epithiostearamide.
 30. The composition of claim 28 wherein the extreme pressure component is N-(2-(9,10-epithiostearoyloxy)ethyl)-9,10-epithiostearamide.
 31. The composition of claim 28 wherein the extreme pressure component is 1,3-bis(9,10-epithiostearoyloxy)propane.
 32. The composition of claim 28 wherein the extreme pressure component is 1,3-di(9,10-epithiostearoyl)hexahydropyrimidine.
 33. The composition of claim 28 wherein the extreme pressure component is 2-ethoxyethyl 9,10-epithiostearate.
 34. The composition of claim 28 wherein the extreme pressure component is 2-(2-ethoxyethoxy)ethyl 9,10-epithiostearate.
 35. The composition of claim 28 wherein the extreme pressure component is 2-ethoxyphenyl 9,10-epithiostearate.
 36. The composition of claim 28 wherein the extreme pressure component is 4-methoxyphenyl 9,10-epithiostearate.
 37. The composition of claim 28 wherein the extreme pressure component is 1,3-bis(9,10-epithiostearoyl)-imidazolidine.
 38. The composition of claim 28 wherein the extreme pressure component is epithioated soybean oil.
 39. The composition of claim 28 wherein the extreme pressure component is 9,10-epithiostearyl 9,10-epithiostearate.
 40. The composition of claim 28 wherein the extreme pressure component is 9,10-epithiostearyl pentachlorostearate.
 41. The composition of claim 28 wherein the extreme pressure component is 9,10-epithiostearoyl terminated sebacic acid-1,3-propanediol polyester. 